Eastern Shore Luxury Holidays 2026

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Top Luxury Eastern Shore Hotels

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

2 hours drive from Ocean City Boardwalk

Stay at this luxury hotel in St. Michaels. Enjoy free Wi-Fi, free valet parking and a full-service spa. Our guests praise the helpful staff in their reviews. ...

9.6/10 Exceptional! (397 reviews)

"Amazing experience highly recommend"

Reviewed on 16 Aug 2026

Inn at 202 Dover

202 East Dover Street Easton MD

2 hours drive from Ocean City Boardwalk

Stay at this luxury inn in Easton. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Avalon Theatre and Customs House are located ...

Lighthouse Club Hotel

200 56th Street Ocean City MD

8 min drive from Ocean City Boardwalk

Stay at this luxury hotel in Ocean City. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...

9.4/10 Exceptional! (732 reviews)

"The hotel was beautiful, the location was peaceful, and the staff was so kind. We will definitely be staying here again."

Reviewed on 18 Aug 2026

See all 7,731 properties in Eastern Shore

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.